CA1340950C - Process and agents for phosphorylation - Google Patents

Process and agents for phosphorylation

Info

Publication number: CA1340950C
Authority: CA; Canada
Prior art keywords: denotes; iii; group; formula; different
Prior art date: 1985-03-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA000503382A

Other languages

English (en)

French (fr)

Inventor

Joachim Engels

Eugen Uhlmann

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-03-06

Filing date

1986-03-05

Publication date

2000-04-11

1986-03-05 Application filed by Hoechst AG filed Critical Hoechst AG

2000-04-11 Application granted granted Critical

2000-04-11 Publication of CA1340950C publication Critical patent/CA1340950C/en

2017-04-11 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 15
230000008569 process Effects 0.000 title claims description 11
238000006366 phosphorylation reaction Methods 0.000 title description 8
230000026731 phosphorylation Effects 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 41
239000003153 chemical reaction reagent Substances 0.000 claims abstract description 16
230000000865 phosphorylative effect Effects 0.000 claims abstract description 16
-1 cyano, phenyl Chemical group 0.000 claims description 37
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
108091034117 Oligonucleotide Proteins 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
239000002777 nucleoside Substances 0.000 claims description 7
239000002773 nucleotide Substances 0.000 claims description 7
125000003729 nucleotide group Chemical group 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
229930195733 hydrocarbon Natural products 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
239000004215 Carbon black (E152) Substances 0.000 claims description 5
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
229910052711 selenium Chemical group 0.000 claims description 4
239000011669 selenium Chemical group 0.000 claims description 4
235000000346 sugar Nutrition 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000001931 aliphatic group Chemical class 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
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230000001590 oxidative effect Effects 0.000 claims description 3
239000002157 polynucleotide Substances 0.000 claims description 3
150000003431 steroids Chemical class 0.000 claims description 3
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims description 2
150000004982 aromatic amines Chemical class 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
150000002989 phenols Chemical class 0.000 claims description 2
150000003904 phospholipids Chemical class 0.000 claims description 2
125000005936 piperidyl group Chemical group 0.000 claims description 2
108091033319 polynucleotide Proteins 0.000 claims description 2
102000040430 polynucleotide Human genes 0.000 claims description 2
150000008163 sugars Chemical class 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical group [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 claims 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 1
229910019142 PO4 Inorganic materials 0.000 abstract description 12
239000010452 phosphate Substances 0.000 abstract description 11
239000000126 substance Substances 0.000 abstract description 7
238000003379 elimination reaction Methods 0.000 abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
230000008030 elimination Effects 0.000 abstract description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract description 3
238000003776 cleavage reaction Methods 0.000 abstract description 2
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 abstract description 2
150000001412 amines Chemical class 0.000 abstract 1
JRPHGDYSKGJTKZ-UHFFFAOYSA-N selenophosphoric acid Chemical class OP(O)([SeH])=O JRPHGDYSKGJTKZ-UHFFFAOYSA-N 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 18
150000003254 radicals Chemical class 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000002585 base Substances 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 9
238000004679 31P NMR spectroscopy Methods 0.000 description 8
235000021317 phosphate Nutrition 0.000 description 8
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125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 6
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ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 6
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BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
229930024421 Adenine Natural products 0.000 description 1
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 1
DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 1
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical group CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
HUJVVLRFPMDFHF-UHFFFAOYSA-N Cl.Cl.OP(O)OCCC1=CC=C([N+]([O-])=O)C=C1 Chemical compound Cl.Cl.OP(O)OCCC1=CC=C([N+]([O-])=O)C=C1 HUJVVLRFPMDFHF-UHFFFAOYSA-N 0.000 description 1
102100033195 DNA ligase 4 Human genes 0.000 description 1
101000927810 Homo sapiens DNA ligase 4 Proteins 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
102000001253 Protein Kinase Human genes 0.000 description 1
108091081062 Repeated sequence (DNA) Proteins 0.000 description 1
101100514056 Rhodobacter capsulatus modD gene Proteins 0.000 description 1
108091028664 Ribonucleotide Proteins 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
IEANINPXXMLCGC-UHFFFAOYSA-N [di(propan-2-yl)amino]phosphonous acid dihydrochloride Chemical compound Cl.Cl.CC(C)N(C(C)C)P(O)O IEANINPXXMLCGC-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
229960000643 adenine Drugs 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
BLORRZQTHNGFTI-ZZMNMWMASA-L calcium-L-ascorbate Chemical compound [Ca+2].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] BLORRZQTHNGFTI-ZZMNMWMASA-L 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000009850 completed effect Effects 0.000 description 1
238000010276 construction Methods 0.000 description 1
239000005289 controlled pore glass Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
229940104302 cytosine Drugs 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000006642 detritylation reaction Methods 0.000 description 1
125000004188 dichlorophenyl group Chemical group 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000727 fraction Substances 0.000 description 1
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
AFQIYTIJXGTIEY-UHFFFAOYSA-N hydrogen carbonate;triethylazanium Chemical compound OC(O)=O.CCN(CC)CC AFQIYTIJXGTIEY-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
230000000415 inactivating effect Effects 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
150000002634 lipophilic molecules Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
150000003013 phosphoric acid derivatives Chemical group 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000006308 propyl amino group Chemical group 0.000 description 1
108060006633 protein kinase Proteins 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
108091008146 restriction endonucleases Proteins 0.000 description 1
239000002342 ribonucleoside Substances 0.000 description 1
239000002336 ribonucleotide Substances 0.000 description 1
125000002652 ribonucleotide group Chemical group 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000010532 solid phase synthesis reaction Methods 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
229940104230 thymidine Drugs 0.000 description 1
125000002480 thymidyl group Chemical group 0.000 description 1
229940113082 thymine Drugs 0.000 description 1
229940055764 triaz Drugs 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
239000001226 triphosphate Substances 0.000 description 1
235000011178 triphosphate Nutrition 0.000 description 1
SCXZATZIVUFOFT-UHFFFAOYSA-N undec-5-ene Chemical compound [CH2]CCCC=CCCCCC SCXZATZIVUFOFT-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/146—Esters of phosphorous acids containing P-halide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2408—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyalkyl compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2429—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of arylalkanols
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/26—Amides of acids of phosphorus containing P-halide groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
General Health & Medical Sciences (AREA)
Biotechnology (AREA)
Engineering & Computer Science (AREA)
Genetics & Genomics (AREA)
Steroid Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Luminescent Compositions (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000503382A 1985-03-06 1986-03-05 Process and agents for phosphorylation Expired - Fee Related CA1340950C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP3507881.2		1985-03-06
DE19853507881 DE3507881A1 (de)	1985-03-06	1985-03-06	Verfahren und mittel zur phosphorylierung

Publications (1)

Publication Number	Publication Date
CA1340950C true CA1340950C (en)	2000-04-11

Family

ID=6264335

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000503382A Expired - Fee Related CA1340950C (en)	1985-03-06	1986-03-05	Process and agents for phosphorylation

Country Status (17)

Country	Link
US (1)	US5039796A (de)
EP (1)	EP0195277B1 (de)
JP (2)	JPH0643433B2 (de)
KR (1)	KR940005338B1 (de)
AT (1)	ATE44151T1 (de)
AU (1)	AU596091B2 (de)
CA (1)	CA1340950C (de)
DE (2)	DE3507881A1 (de)
DK (1)	DK174772B1 (de)
ES (1)	ES8801293A1 (de)
FI (1)	FI81806C (de)
GR (1)	GR860600B (de)
HU (1)	HU202247B (de)
IE (1)	IE58874B1 (de)
IL (1)	IL78033A (de)
PT (1)	PT82139B (de)
ZA (1)	ZA861629B (de)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5332845A (en) *	1985-03-28	1994-07-26	Chiron Corporation	Phosphorylating reagents
US5071974A (en) *	1986-10-31	1991-12-10	Amoco Corporation	Compositions and methods for the synthesis of oligonucleotides having 5'-phosphorylated termini
US5585481A (en) *	1987-09-21	1996-12-17	Gen-Probe Incorporated	Linking reagents for nucleotide probes
US6031091A (en) *	1987-09-21	2000-02-29	Gen-Probe Incorporated	Non-nucleotide linking reagents for nucleotide probes
SE8802574D0 (sv) *	1988-07-08	1988-07-08	Wallac Oy	Oligonucleotide hybridization probes and means for the synthesis of the most preferred probes
US5380835A (en) *	1991-06-07	1995-01-10	Abbott Laboratories	Silyl phosphorylating reagents and methods of using them
US5872244A (en) *	1994-09-02	1999-02-16	Andrew C. Hiatt	3' protected nucleotides for enzyme catalyzed template-independent creation of phosphodiester bonds
US6232465B1 (en)	1994-09-02	2001-05-15	Andrew C. Hiatt	Compositions for enzyme catalyzed template-independent creation of phosphodiester bonds using protected nucleotides
US5990300A (en) *	1994-09-02	1999-11-23	Andrew C. Hiatt	Enzyme catalyzed template-independent creation of phosphodiester bonds using protected nucleotides
US5763594A (en) *	1994-09-02	1998-06-09	Andrew C. Hiatt	3' protected nucleotides for enzyme catalyzed template-independent creation of phosphodiester bonds
US6214987B1 (en)	1994-09-02	2001-04-10	Andrew C. Hiatt	Compositions for enzyme catalyzed template-independent formation of phosphodiester bonds using protected nucleotides
US5808045A (en) *	1994-09-02	1998-09-15	Andrew C. Hiatt	Compositions for enzyme catalyzed template-independent creation of phosphodiester bonds using protected nucleotides
US6184347B1 (en)	1998-11-19	2001-02-06	Agilent Technologies Inc.	Minimization of blooming in high-density arrays by using reactive wash reagents
AU2998800A (en)	1999-03-24	2000-10-09	Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The	N-acylphosphoramidites and their use in oligonucleotide synthesis
WO2003048179A2 (en) *	2001-12-03	2003-06-12	The Government Of The United States Of America, Represented By The Secretary Of The Department Of Health And Human Services	Thermolabile hydroxyl protecting groups and methods of use
GB0304371D0 (en)	2003-02-26	2003-04-02	Solexa Ltd	DNA Sequence analysis
US9809824B2 (en)	2004-12-13	2017-11-07	The United States Of America, Represented By The Secretary, Department Of Health And Human Services	CpG oligonucleotide prodrugs, compositions thereof and associated therapeutic methods
DE102009012640A1 (de) *	2009-03-09	2010-09-30	Freie Universität Berlin	Mit einer Phosphoamidatgruppe modifizierte Verbindung und deren Verwendung
WO2016006381A1 (ja) *	2014-07-09	2016-01-14	日本電気株式会社	非水電解液及びリチウムイオン二次電池

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1075584B (de) *		1960-02-18	Hooker Chemical Corporation, Niagara Falls, N. Y. (V. St. A.)	Verfahren zur Herstellung von tertiären aliphatischen Estern der phosphorigen Säure
BE627406A (de) *	1962-01-29
US4321365A (en) *	1977-10-19	1982-03-23	Research Corporation	Oligonucleotides useful as adaptors in DNA cloning, adapted DNA molecules, and methods of preparing adaptors and adapted molecules
US4415732A (en) *	1981-03-27	1983-11-15	University Patents, Inc.	Phosphoramidite compounds and processes
NL8302353A (nl)	1983-07-01	1985-02-01	Stichting Katholieke Univ	Fosforyleringsmiddel; werkwijze voor het bereiden daarvan; werkwijze voor het fosforyleren van een organische hydroxyl- of amineverbinding.
DE3484719D1 (de)	1983-08-19	1991-07-25	Gen Electric	Modifizierte polyesterzusammensetzung.
DE3678988D1 (de) *	1985-03-28	1991-06-06	Chiron Corp	Reinigung von synthetischen oligomeren.

1985
- 1985-03-06 DE DE19853507881 patent/DE3507881A1/de not_active Withdrawn
1986
- 1986-02-22 EP EP86102311A patent/EP0195277B1/de not_active Expired
- 1986-02-22 AT AT86102311T patent/ATE44151T1/de not_active IP Right Cessation
- 1986-02-22 DE DE8686102311T patent/DE3664047D1/de not_active Expired
- 1986-03-04 HU HU86889A patent/HU202247B/hu unknown
- 1986-03-04 FI FI860905A patent/FI81806C/fi not_active IP Right Cessation
- 1986-03-04 IL IL78033A patent/IL78033A/xx unknown
- 1986-03-04 GR GR860600A patent/GR860600B/el unknown
- 1986-03-04 ES ES552614A patent/ES8801293A1/es not_active Expired
- 1986-03-05 JP JP61046486A patent/JPH0643433B2/ja not_active Expired - Lifetime
- 1986-03-05 DK DK198601009A patent/DK174772B1/da not_active IP Right Cessation
- 1986-03-05 ZA ZA861629A patent/ZA861629B/xx unknown
- 1986-03-05 KR KR860001541A patent/KR940005338B1/ko not_active Expired - Lifetime
- 1986-03-05 CA CA000503382A patent/CA1340950C/en not_active Expired - Fee Related
- 1986-03-05 IE IE57986A patent/IE58874B1/en not_active IP Right Cessation
- 1986-03-05 AU AU54311/86A patent/AU596091B2/en not_active Expired
- 1986-03-05 PT PT82139A patent/PT82139B/pt unknown
1989
- 1989-08-21 US US07/396,803 patent/US5039796A/en not_active Expired - Lifetime
1993
- 1993-09-29 JP JP5242250A patent/JP2549495B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE3507881A1 (de)	1986-09-11
JP2549495B2 (ja)	1996-10-30
EP0195277A1 (de)	1986-09-24
FI860905A0 (fi)	1986-03-04
JPH06228172A (ja)	1994-08-16
IE860579L (en)	1986-09-06
AU596091B2 (en)	1990-04-26
ATE44151T1 (de)	1989-07-15
HU202247B (en)	1991-02-28
ES552614A0 (es)	1987-12-16
ES8801293A1 (es)	1987-12-16
FI81806B (fi)	1990-08-31
IL78033A0 (en)	1986-07-31
PT82139A (de)	1986-04-01
HUT40675A (en)	1987-01-28
DK100986D0 (da)	1986-03-05
US5039796A (en)	1991-08-13
IL78033A (en)	1990-12-23
PT82139B (pt)	1988-07-29
EP0195277B1 (de)	1989-06-21
DK174772B1 (da)	2003-10-27
KR860007273A (ko)	1986-10-10
JPS61207397A (ja)	1986-09-13
IE58874B1 (en)	1993-12-01
FI81806C (fi)	1990-12-10
FI860905L (fi)	1986-09-07
JPH0643433B2 (ja)	1994-06-08
GR860600B (en)	1986-07-07
DE3664047D1 (en)	1989-07-27
KR940005338B1 (en)	1993-06-17
DK100986A (da)	1986-09-07
AU5431186A (en)	1986-10-16
ZA861629B (en)	1986-10-29

Legal Events

Date	Code	Title	Description
2016-05-23	MKLA	Lapsed	Effective date: 20160411

Publication	Publication Date	Title
CA1340950C (en)	2000-04-11	Process and agents for phosphorylation
US5847106A (en)	1998-12-08	Monomeric and dimeric nucleosides with silyl-containing diamino phosphorous linkages
US4816571A (en)	1989-03-28	Chemical capping by phosphitylation during oligonucleotide synthesis
JP2552048B2 (ja)	1996-11-06	ヌクレオチド鎖合成用試薬
US5571902A (en)	1996-11-05	Synthesis of oligonucleotides
US4959463A (en)	1990-09-25	Intermediates
CA2011430C (en)	2000-06-20	Method and reagent for sulfurization of organophosphorous compounds
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